Hydrazine → 3-amino-N-(2-chlorobenzyl)-2,2-dimethylpropanamide

HRID 655959Notes

Reaction equation

HRID 655959 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6](=[O:22])[C:7]([CH3:21])([CH3:20])[CH2:8][N:9]1C(=O)C2C(=CC=CC=2)C1=O.NN>CO>[NH2:9][CH2:8][C:7]([CH3:21])([CH3:20])[C:6]([NH:5][CH2:4][C:3]1[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=1[Cl:1])=[O:22]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59778496N-(2-chlorobenzyl)-3-(1,3-dioxoisoindolin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 597784043-amino-N-(2-chlorobenzyl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-chlorobenzyl)-3-(1,3-dioxoisoindolin-2-yl)-2,2-dimethylpropanamide (0.50 g, 1.35 mmol) in methanol (5 mL) was added hydrazine (423 μL, 13.5 mmol, 10 equiv.). The reaction mixture was stirred overnight. The crude mixture was concentrated. The resulting residue was dried in vacuum to give 3-amino-N-(2-chlorobenzyl)-2,2-dimethylpropanamide, which was used without further purification. LRMS (M+H+) m/z 241.1.

Workup

  1. concentrationThe crude mixture was concentrated
  2. customThe resulting residue was dried in vacuum

Sources & evidence

ORD record
ord-2e839ab4901d47c09e9a17f884e7b1dc
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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